Methyl iodide → methyl (2S)-2-[(4-fluorophenyl)sulfonyl-methyl-amino]-3-hydroxy-propanoate
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:17][OH:18])[C:13]([O:15][CH3:16])=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[C:19]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH3:19])[C@@H:12]([CH2:17][OH:18])[C:13]([O:15][CH3:16])=[O:14])(=[O:9])=[O:10])=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A solution of 2A (2 g, 7.2 mmol) in DMF (20 mL) was added with an. K2CO3 (1.5 mol eq, 1.49 g) and, after few minutes, iodomethane (1.2 mol eq, 0.8 ml) was added and the mixture heated at 50° C. for 12 h. The solvent was removed under reduced pressure, water was added to the residue (100 mL) and the aqueous phase extracted with EtOAc (3×40 mL). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to obtain 3A as a pale yellow oil (2.3 g, quantitative yield). 1HNMR (DMSO, 200 MHz) δ 2.82 (s, 3H), 3.50 (s, 3H), 3.69 (m, 3H), 4.60 (t, 1H, J=6), 5.12 (t, 1H, J=6.1), 7.44 (m, 2H), 7.83 (m, 2H).
Workup
- customThe solvent was removed under reduced pressure, water
- additionwas added to the residue (100 mL)
- extractionthe aqueous phase extracted with EtOAc (3×40 mL)
- dry with materialThe combined organic phases were dried over Na2SO4
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-020e109ee853468da21a27a4d727eed5
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409864B2
Reaction notes
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